The Owner's Playbook

Carol Dewey
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The Owner’s Playbook explores what it really means to grow, prepare, and eventually exit a business. Hosted by Carol Dewey, founder of Clarus Advisory Partners, the show highlights the realities every business owner will face—including the importance of transferable value, the factors that shape a successful exit, and the personal vision behind every end game.

  1. Oct 1

    Your Business Is Worth $10 Million... But What Do You Actually Keep?

    A $10 million business offer sounds like financial freedom. But how much of that money actually makes it into your pocket? In this episode of The Owner’s Playbook, Carol Dewey explores the difference between a company's headline valuation and the actual wealth a business owner takes home after a sale. Through Sarah's journey, she explains how deal structures, taxes, debt, and transaction expenses can significantly affect the financial outcome of a business exit. Key TakeawaysWhy a $10 million sale doesn't necessarily mean $10 million in personal wealthHow debt, transaction costs, taxes, and contingent payments affect net proceedsWhy deal structure matters just as much as the purchase priceHow a hypothetical $10 million offer could result in approximately $5.45 million in immediate net proceedsWhy business owners should determine their financial freedom number before negotiating an exitThe difference between the value gap and the wealth gapWhy early exit planning creates more opportunities to protect and preserve wealth A successful business exit isn't necessarily the one with the highest selling price. It's the one that provides the financial security, freedom, and opportunities you envisioned when you started building your company. The question isn't just, "What is my business worth?" It's, "What do I actually get to keep?" Listen & ConnectThe Owner’s Playbook – Official Podcast Apple Podcasts – The Owner’s Playbook

  2. Sep 17

    The Three Tax Buckets Every Business Owner Should Build Before the Exit

    Building wealth is one challenge. Creating flexibility around how that wealth eventually supports your life is another. In this episode of The Owner’s Playbook, Carol Dewey explores why business owners should think beyond simply accumulating assets and start considering how those assets may eventually be taxed. She introduces three broad tax buckets—taxable, tax-deferred, and tax-advantaged—and explains how having different sources of future income can create greater flexibility before and after a business exit. Key TakeawaysThe difference between accumulating wealth and planning for future distributionsThe three tax buckets: taxable, tax-deferred, and tax-advantagedWhy tax-deferred doesn’t necessarily mean tax-freeHow multiple tax buckets can provide greater flexibility around future incomeWhy tax diversification should begin before the year you plan to exitWhy the lowest tax bill today isn’t always the best long-term financial outcomeHow tax planning can support both personal freedom and greater negotiating strength when selling a business Tax strategy isn’t simply about finding the biggest deduction this year. It’s about coordinating decisions across your lifetime and creating options for an uncertain future. Financial freedom is strengthened by options—and tax flexibility is another form of optionality. Listen & ConnectThe Owner’s Playbook: Listen to The Owner’s Playbook Apple Podcasts – The Owner’s Playbook: Listen on Apple Podcasts

  3. Sep 3

    Business Rich, Cash Poor: When Your Net Worth Is Trapped Inside Your Company

    A successful business can make you wealthy on paper—but does that wealth actually give you financial freedom? In this episode of The Owner’s Playbook, Carol Dewey explores the difference between net worth and financial independence. Through Sarah’s continuing journey, she explains why having most of your wealth concentrated inside your company can limit your flexibility—and why business owners should intentionally begin building wealth outside the enterprise. Key TakeawaysWhy high net worth doesn’t automatically mean financial independenceThe risks of having your business serve as your largest asset, income source, and retirement planWhy enterprise value is not the same as family wealthHow liquidity and diversification can create greater financial flexibilityWhy relying on a future business sale can create another form of dependenceHow intentionally transferring wealth from the business balance sheet to the family balance sheet can create more optionsWhy business owners should track personal financial independence alongside business performance Your business may be the greatest wealth-creation engine you ever own. But ultimately, that wealth should create something beyond the company: security, choices, opportunities, and freedom. Listen & ConnectThe Owner’s Playbook: Listen to The Owner’s Playbook Apple Podcasts – The Owner’s Playbook: Listen on Apple Podcasts ⭐ Leave a Review: Share Your Review

  4. Aug 20

    The Day Everything Changed: Protecting What You've Built Before It's Too Late

    What happens to your business, income, family, and employees if you suddenly can’t work for six months? In this episode of The Owner’s Playbook, Carol Dewey explores the risks successful business owners often overlook while they’re focused on growth. Through Sarah’s continuing story, Carol explains why protecting what you’ve built requires more than insurance—it requires coordinated planning across your business, legal documents, taxes, personal finances, and family. Key TakeawaysWhy optimism alone is not a risk-management strategyHow to identify vulnerabilities before an unexpected event exposes themThe four layers of protection: business, owner, family, and legacyWhy insurance, legal, tax, and financial planning must work togetherHow owner disability, key-person loss, lawsuits, cyber risk, and other disruptions can affect business valueWhy risk planning should focus on consequences—not just probability The goal isn’t to worry about everything that could go wrong. It’s to build enough resilience that one unexpected event doesn’t undo everything you’ve spent years creating. Listen & ConnectThe Owner’s Playbook: Listen to The Owner’s Playbook Apple Podcasts – The Owner’s Playbook: Listen on Apple Podcasts

  5. Aug 7

    Stop Building a Business... Start Building an Enterprise

    There’s a difference between owning a successful business and building an enterprise that can create value without depending on you. In this episode of The Owner’s Playbook, Carol Dewey explores the shift from being the constant firefighter inside your company to becoming the architect of an enterprise. Through Sarah’s continuing journey, Carol explains how systems, leadership, delegation, and documented processes can reduce owner dependence, increase transferable value, and create greater personal freedom. Key TakeawaysThe difference between building a business and building an enterpriseWhy buyers purchase predictable, transferable value—not an owner’s hard workHow moving from “firefighter” to “architect” changes the way you leadWhy systems help create consistency, confidence, and freedomHow reducing owner dependence can increase enterprise valueWhy freedom is something business owners intentionally build—not something they simply find A business can create income. An enterprise creates choices, freedom, and transferable value. Listen & Connect🎧 The Owner’s Playbook: Listen to The Owner’s Playbook 🍎 Apple Podcasts – The Owner’s Playbook: Listen on Apple Podcasts

  6. Jul 23

    You Don't Own a Business Until the Business Can Survive Without You

    You may own your company on paper—but if the business cannot function without your daily involvement, how much freedom do you really have? In this episode of The Owner’s Playbook, Carol Dewey explores one of the biggest threats to both business value and personal freedom: owner dependence. She explains why businesses built around one indispensable owner can become less attractive to buyers and shares practical ways to begin building a company that can thrive without you. Key TakeawaysWhy owner dependence can reduce business value and personal freedomHow buyers view an owner-dependent company as a greater riskFour questions that can reveal how dependent your business is on youWhy systems, documentation, leadership, and delegation matterHow reducing operational bottlenecks can strengthen transferabilityThree practical steps to start making your business less dependent on you The goal isn't to become less important. It's to become less indispensable—building a business that gives you choices, creates transferable value, and supports the freedom you originally set out to achieve. Listen & ConnectThe Owner’s Playbook Apple Podcasts Leave a Review

  7. Jul 9

    The Wealth Trap of Successful Business Owners

    It’s possible to build a successful company, accumulate significant wealth, and still feel financially trapped. In this episode of The Owner’s Playbook, Carol Dewey explores the “wealth trap” many successful business owners experience when too much of their wealth, income, and future security remain tied to the business. She explains why revenue, wealth, and freedom are not the same—and why the ultimate goal of wealth is creating options. Key TakeawaysWhy revenue, wealth, and financial freedom are three different thingsThe risks of having most of your net worth concentrated in your businessFour warning signs that you may be caught in the wealth trapWhy building a business and preserving wealth require different skill setsThe importance of transferable value, diversification, and liquidityWhy true wealth ultimately comes down to having control over your time, choices, and future The goal of business ownership isn’t simply to create income or accumulate wealth. It’s to create options—and those options are what ultimately create freedom. Listen & ConnectThe Owner’s Playbook: Apple Podcasts ⭐ Leave a Review

  8. Jun 25

    The Silent Business Partner Taking 30%-50% of Your Profits

    In this episode of The Owner’s Playbook, Carol Dewey discusses one of the most overlooked threats to a business owner’s long-term wealth: unnecessary taxes. While many owners focus heavily on revenue, growth, and profit, fewer pay attention to how much of that success actually reaches their personal balance sheet. Carol explains the “success trap,” where a business may grow larger and more profitable, yet the owner feels more pressure, less freedom, and greater financial complexity. She introduces the Owner’s Wealth Triangle: business value, tax efficiency, and personal freedom, emphasizing that all three must work together to create lasting wealth. The episode also explores common ways business owners lose wealth, including excessive taxation, unnecessary risk, poor succession planning, and lack of liquidity. Carol encourages owners to think beyond annual tax filing and begin treating tax strategy as part of long-term wealth strategy. Key takeaways include knowing your true effective tax rate, asking your advisory team about tax planning opportunities over the next three years, and understanding how much of your net worth exists outside your business. Ultimately, success is not only measured by what you build, but by what you keep, enjoy, and pass on.

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About

The Owner’s Playbook explores what it really means to grow, prepare, and eventually exit a business. Hosted by Carol Dewey, founder of Clarus Advisory Partners, the show highlights the realities every business owner will face—including the importance of transferable value, the factors that shape a successful exit, and the personal vision behind every end game.

Information

  • Creator
    Carol Dewey
  • Years Active
    2025 - 2026
  • Episodes
    26
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Carol Dewey
  • Show Website
    The Owner's Playbook